Buchwald–Hartwig amination, record ord-fa6037d0d8a544539857cac2da5223a4
One recorded run of this reaction. Below is what the source recorded, and nothing added to it.
What was in the flask
| Role | Species | Formula | Yield |
|---|---|---|---|
| Reactant | 3-Bromoanisole | C₇H₇BrO | |
| Reactant | 4-Cyanopiperidine | C₆H₁₀N₂ | |
| Reagent | lithium bis(trimethylsilyl)azanide | C₆H₁₈LiNSi₂ | |
| Catalyst | 2,8,9-Triisobutyl-2,5,8,9-tetraaza-1-phosphabicyclo(3.3.3)undecane | C₁₈H₃₉N₄P | |
| Catalyst | Palladium (II) acetate | C₄H₈O₄Pd | |
| Solvent | Toluene | C₇H₈ | |
| Product | 1-(3-Methoxyphenyl)piperidine-4-carbonitrile | C₁₃H₁₆N₂O | 54.48% |
Conditions
- Temperature
- 100 °C
Yield
- 54% of 1-(3-Methoxyphenyl)piperidine-4-carbonitrile.
Procedure
Copied from the source record, unedited
piperidine-4-carbonitrile (0.353 g, 3.21 mmol); 1-bromo-3-methoxybenzene (0.339 mL, 2.67 mmol) and diacetoxypalladium (0.120 g, 0.53 mmol) were thoroughly placed under an inert atmoshere. To this was added 2,8,9-triisobutyl-2,5,8,9-tetraaza-1-phosphabicyclo[3.3.3]undecane (0.037 g, 0.11 mmol); LITHIUM BIS(TRIMETHYLSILYL)AMIDE (6.15 mL, 6.15 mmol) and toluene (10 mL). The resultant mixture was stirred overnight at 100 °C (suspect that it did not need overnight. Equal vol of DCM was added and the reaction mixture filtered. Removal of the solvent under reduced pressure gave a dark brown gum. The crude product was purified by flash Silica chromatography {CombiFlash Companion - Presearch Ltd}, column size = 12 g , flow rate = 30 ml / min, elution gradient 0 to 30% EtOAc in isohexane over 10 m
The source
This record comes from experimental reaction archive (ord-fa6037d0d8a544539857cac2da5223a4). Open the source and check it against what is on this page.
experimental reaction archive record ord-fa6037d0d8a544539857cac2da5223a4 from dataset "750 AstraZeneca ELN dataset" (url: https://chemrxiv.org/engage/chemrxiv/article-details/60c9e3f37792a23bfdb2d471). No atom mapping is provided by the source.
How to read this record
This is one experiment, not a rule. It says that on one occasion these species were combined under these conditions and this came out. It does not say the reaction will give the same result on your substrate, and nothing on the page has been generalised into a claim that it would.
The pathway is a separate question, kept on separate pages. A mechanism here is the canonical arrow pushing for a class, run on real structures and labelled rule-derived. It is not evidence, and this record is not a mechanism.